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Outdoor Activities in Westchester County, NY the Whole Family Will Love

By September 6, 2019September 14th, 2023No Comments
Outdoor Activities in Westchester County, NY

We don’t know about you, but for the team at 914 Smiles, the summer holidays went by in the blink of an eye. But even though we love warm, sunny days as much as our Tarrytown pediatric and orthodontic patients, we’re always ready to welcome sweater weather with open arms. Fortunately, there are still plenty of opportunities to get outside and enjoy the beauty of fall. As the leaves start to change color, here’s a list of the best outdoor family activities in Westchester County and beyond.

1. Visit the New York Renaissance Faire


Every Saturday and Sunday until October 6th, Sterling Forest transforms into Elizabethan England, with games, rides, food, performances and more. Catch a jousting match, indulge on turkey legs and sweet treats, or simply stroll through the Majestic Groves and take it all in. The Faire is open from 10am to 7pm. Admission is $29.95 for adults and $13 for kids, but discount coupons are also available.

2. Explore the Harvest Festival at Bethel Woods

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It wouldn’t really be autumn without hayrides and corn mazes. Load up the kids and head to Bethel Woods on Sundays in September for the Harvest Festival, an event that features local vendors and celebrates everything that fall has to offer. There’s live music, food trucks, a farmers market, horses and more. This is sure to be your children’s favorite thing to do this fall in Westchester County. Admission is free for everyone and doors open at 11am.

3. Shop at the Tarrytown & Sleepy Hollow Farmers Market

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Open every Saturday from Memorial Day to Thanksgiving, the TaSH Farmers Market is one of the best outdoor activities for families in Tarrytown and Sleepy Hollow. It was voted the “Best of Winchester” in 2017 for good reason: this vibrant market offers autumn fun for the whole family, from face painting and craft tables, to yoga classes and storytime, and so much more. Entry is always free and you can park for free across the street at John Paulding School. The market is open from 8:30am to 2pm.

4. Witness the Sleepy Hollow Experience


Tarrytown becomes the backdrop for everyone’s favorite ghost story this October and November. Watch the tale of the Headless Horseman come to life under the stars at Washington Irving’s Sunnyside. The outdoor performances take place every Friday to Sunday in October and the first weekend of November at 6:30pm and 8:30pm. The show is only 60 minutes long, so it’s sure to captivate the attention of even the youngest audience members. Buy your tickets now before they sell out!

5. Experience a Westchester County Haunted House

Thrill seekers, this one’s for you. Westchester County does Halloween right with dozens of scary and ghoulish haunted houses. From family-friendly events to downright terrifying haunts, there’s a haunted house for everyone from scaredy cats to the bravest kids. Check out this handy list of haunted events throughout Westchester County — if you dare!

6. Admire the Fall Foliage at One of Tarrytown’s Beautiful Parks

If you’re looking for free family activities in Tarrytown, Sleepy Hollow and the surrounding area, all you have to do is take a stroll through one of Westchester County’s stunning parks. New York has never been more beautiful than in autumn, when the leaves are turning orange and red, and every park looks like it’s glowing. October and November are prime leaf peeping months, but be sure to check the New York Fall Foliage Report to find the best spot. Our favorite parks are Kingsland Point Park and Old Croton Aqueduct State Historic Park. If you go, don’t forget to hashtag #NYLovesFall on Instagram!

7. Attend the 18th Annual Tarrytown Halloween Parade

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Winner of the “Best of Winchester” for five years running, the Tarrytown Halloween Parade is an outdoor activity for families that can’t be missed. There will be costumes, live performances, food, a DJ, a block party and more, guaranteeing fun for kids and adults of all ages. This year’s parade kicks off on Saturday, October 26th, at Patriots Park. Bring the kids and make this Halloween season one to remember.

8. Take the Kids to the Sleepy Hollow Craft & Street Fair

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Everyone’s favorite fall fair is back this year on October 12th and as usual, it promises to be a day of family fun. Every year, the fair showcases over 100 local vendors from food, crafts, jewelry, clothes, art, accessories and more. The Sleepy Hollow Craft & Street Fair runs from 10am to 5pm on Beekman Ave.

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9. Attend the Great Jack O’Lantern Blaze

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This all ages Halloween extravaganza is a must-see event for families in Westchester. There will be over 7,000 carved pumpkins on display, a haunted carousel, planetarium and so much more. As one of the Hudson Valley’s most loved family fall activities, you’ll want to be sure to get tickets early. Admission is $23 for adults and $17 for kids ages 3 to 17.

10. Step Back in Time at Horseman’s Hollow


Take a journey to the past to 18th century Sleepy Hollow, the home the infamous Headless Horseman. Philipsburg Manor will be transformed into a haunted Halloween landscape, from the cemetery to the tavern to Old Dutch Church. Horseman’s Hollow isn’t for the faint of heart (or for little ones), but brave adults and kids ages 10 and up may enter … if you dare.

Dr. Kothari

Author Dr. Kothari

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